You’ve probably heard of Instagram’s newly famed motivational speaker, “Gary Vee,” or @garyvee. It’s hard to miss his unfiltered, no-BS, “let’s get straight to the point”-type social media mantras like “Bulls*** entrepreneurs cry about the way they want it to be versus reacting to the way it actually is,” and “Getting boo’d makes me competitive as f***.” But don’t let his insta-fame fool you and/or his 3.4+ million followers. Gary Vaynerchuk has been around for more than a minute, and is much (much) more than a motivational speaker. He actually started his first venture—a “very successful baseball card business”—at the mere age of 13. Today, he is the chairman of VaynerX—a media and communications company—and the chief executive officer of VaynerMedia—an advertising agency with four locations, working with Fortune 100 clients. At the ripe age of 42, he continues his entrepreneurial journey full steam ahead, which is when Haute Living was fortunate enough to have the rare opportunity to sit down with Vaynerchuk to discuss all things entrepreneurship, his success, his failures and the future.

Photo Credit: David Drebin

You’d expect someone like Vaynerchuk to turn to another inspirational figure to fuel his fire, but surprisingly, he doesn’t really have a specific one. Rather, his motivation stems from two driving forces he confidently and quickly shares: his parents and the community itself. It was the former of the two, his father, who set him on the right path to become the entrepreneur he is today. In the late 1990s, he took over his father’s $3 million business—a local liquor store. Shortly thereafter, he sprinkled in a bit of calculated risk, a dash of his foresight and just a pinch of creativity into the business and voilà! A short five years later, “Shoppers Discount Liquor” became “Wine Library”—one of the first e-commerce platforms ever for wine—worth $60 million. He credits his father for giving him free rein to build the company in the way he knew how. “When I went into my dad’s business, the truth is, he gave me a ton of autonomy,” begins Vaynerchuk. “That is why I was able to build him a big business.”

Photo Credit: Gary Vaynerchuk

And when it comes to big businesses, it almost seems like Gary Vee has the Midas touch: Everything he gets his hands on turns to gold. Vaynerchuk was an early investor in numerous successful digital companies like Uber, Venmo, Twitter and Facebook. It’s almost uncanny that someone could have the foresight to handpick what would later become some of the biggest companies in the world. So how exactly does he choose from the plethora of platforms that are presented to him? “Two things. Number one, I have to believe in the thesis. When I invested in Venmo in 2009… I thought everybody would have social media accounts. But that’s not what people thought back then. So I have to believe in what’s being said. And number two, I have to believe in him or her, or what I call ‘the jockey.’ It’s all about the jockey for me. When I’ve lost money, it’s because I’ve been right about the thesis, but wrong about the jockey.” When asked to expand on his notion, he divulges some of his past failures. “BlackJet is a company I invested in, which is basically JetSmarter. Same thesis. I was right, but it didn’t become JetSmarter because the jockey didn’t win. Same thing with Yobongo. I was right about the thesis, which was Tinder. I had seen the app Grindr and I thought, ‘That’s definitely going to happen with guys and girls.’ Every app between 2010 and 2012 looked like it, where people met each other within close proximities. But mine didn’t become Tinder. So I was right about the thesis, wrong about the jockey.”

Photo Credit: David Drebin

Playing his own jockey and writing his own thesis, Vaynerchuk has truly become the master of his own brand, likely “because it’s the place where [he has] 100-percent control.” And naturally, big brands attract big brands, which is why some major ones have been seeking him out to collaborate on various projects. One of these major brands is K-Swiss—the sneaker company that he partnered with on his 01 and 02 sneakers, both of which sold out very quickly. “It’s a nostalgic brand that I thought would resonate with my audience,” notes Vaynerchuk, explaining why he opted for a slightly unexpected choice between the major sneaker players in the game. “It was also a real collaboration… And sneakers, as you know, are one of the five, seven or 12 pillars of culture, so surprising the market in that game was an awfully powerful thing for me.” That power will surely carry over to his third and fourth collaborations with the brand, aptly named 03 and 04, coming out later this year. “The 03 and 04, I’m even more involved in,” he says. “I give all the credit to the company’s president, Barney, who sought me out, but I also really wanted to be empathetic to the designers at K-Swiss. I wanted to learn and watch them, but I still wanted to have my fingerprint. Now, I have my handprint on these next ones and eventually, it’ll be my whole hand.”

Photo Credit: Gary Vaynerchuk

But that hand, will of course, first and foremost, continue to feed into his own businesses that are growing so rapidly, clients are actually seeking him out; that’s no easy feat in the world of media and advertising. That role reversal is in large part, most likely a result of Vaynerchuk embodying the qualities and the mentality that he believes, make for a true entrepreneur. “My definition of a true entrepreneur is someone who can’t live without doing their thing and is literally suffocated trying to create it,” he explains.

However, on the flip side, social media has also given rise to the faux entrepreneur—something that Vaynerchuk struggles with. “I talk a lot about ‘stop posting cash, Lamborghinis and private jets’ not because I think one doesn’t deserve it after working hard. But it’s because so many people on Instagram who are posting that stuff are fronting. They’re literally driving to a private plane pad, taking a photo and driving home… But you know what? I think if you’re in the game just for the finer things in life… the bottles, the models and the private planes, I think you’re going to lose and it’s definitely not my definition of an entrepreneur.”

Photo Credit: David Drebin

Now we definitely know that Gary Vee isn’t “fronting.” He’s got millions to his name, a multitude of companies under his belt and a global reach that’s growing by the day. And he knows he’s successful too. “To me, the ultimate success is doing what you want to do every day and having nobody have any impact on that, so I’d say I’m fairly successful.” So why isn’t he throwing around the cash and cruising in Lambos? When asked, he chuckles, ever so slightly. “All that stuff is nice, and I think it’s good to reward yourself for hard work. But I’m not trying to buy the piece of jewelry. I’m trying to buy the whole jewelry company.”